Dec 2014 hotel stay - when to book?

We are cruising out of SJ on 12/27 and looking to stay for a few days beforehand in SJ or close by somewhere. We haven't been to SJ before.

I've checked prices...and they're quite a bit (especially once that pesky 20% resort fee is added). Should I wait to book - are they likely to go down in price yet? Or should I jump on something now because the prices are only likely to increase from here?

Maybe I should book something cancellable now and then try last minute travel dot come or other as we get closer?

In case it's helpful - I want to be on the beach or very close by; there are four of us (including 12yo and 16yo); must have a pool. (I have this plan to be on the beach for Christmas Day - a counterpoint from our usual running around to prep for extended family coming over to our house.)

Thanks for any info or advice!

I started checking pricing way in advance and noted that most were $200 per night, and several required a two-night stay. I got a Hilton Honors Visa card and ended up with a free room at Caribe Hilton. This way, we avoided not only the 2-night minimum, but also that pesky 20% resort fee.

We spent one night before cruise on 20 December 2013. I purchased a room for our family of 4 on Hotwire last May. It was significantly earlier than I would usually book on Hotwire, but it worked out well in the end. We paid $126 plus taxes and fees (including resort fee) for a total of about $179. We ended up with La Concha, which has a pool and beach, and we were upgraded to a suite upon arrival.

I recommend booking a refundable room and then regularly checking Hotwire for something you like. See the sticky thread (above) for Hotwire tips.

We are booked Dec 26-28 prior to our cruise, and I agree the prices a high! We booked 2 nights at the Coral Princess based on a recommendation of a friend. It has good reviews. I think you can get a room for around $170/night.

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We have always had good luck with priceline in San Juan. In 2012 we bid for a while and finally won Caribe Hilton for a couple of days post cruise for $125 per day it was for the 24th, 25th, and 26th of December so you can find better prices but you might have to have some patience with bidding. Also it is a very good idea to have a reservation that is able to cancel. Good luck to you and enjoy your cruise and time in San Juan. It is nice to be there over Christmas.

I'm sailing from SJU Dec 13. I will be flying in a day before and I booked my hotel 2.5 months ago. I booked a Priceline Express Deal and got the La Concha for $162 that includes the resort fee. The rate was $122. I pay the reort fee at checkin/out.

I'm going at the end of November and booked months ago. I priced it for several months before that and except for a sale or two prices never fluctuated. There are some sites like booking dot com where you just need to pay a deposit and can cancel up until pretty much the last minute if that's what you're looking for. I booked a package with two different hotels, first a beachfront at La Concha then El Convento, combined with airfare and saved about $500 booking on Expedia and just paid a deposit equal to the airfare and I think a percentage of the hotel stay. It was a great deal. You might want to check out their packages.